US7309726B2 - Straight-oil finishing composition and fiber yarn treated therewith - Google Patents

Straight-oil finishing composition and fiber yarn treated therewith Download PDF

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US7309726B2
US7309726B2 US10/530,458 US53045805A US7309726B2 US 7309726 B2 US7309726 B2 US 7309726B2 US 53045805 A US53045805 A US 53045805A US 7309726 B2 US7309726 B2 US 7309726B2
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straight
sio
oil
siloxane units
groups
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US20060163523A1 (en
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Mari Wakita
Hisataka Nakashima
Hideki Kobayashi
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DuPont Toray Specialty Materials KK
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Dow Corning Toray Silicone Co Ltd
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/01—Silicones

Definitions

  • the invention relates to a straight-oil finishing composition useful for treating fiber yarn which has improved storage stability and antistatic properties, and a fiber yarn treated with the straight-oil finishing composition.
  • a yarn-treating composition obtained by combining a dimethylsiloxane oil with the product of copolymerization of an MQ-type silicone resin and a DT-type silicone resin (see Kokoku No. Sho 63-12197) is also known.
  • a drawback of the aforementioned product of copolymerization of the silicone resins is that copolymerization of the silicone resin is difficult to control and that viscosity and antistatic properties of the obtained oil-type treatment agent are subject to variations.
  • One object of the invention to provide a straight-oil finishing composition, which has excellent storage stability and antistatic properties.
  • the present invention relates to a straight-oil finishing composition
  • a straight-oil finishing composition comprising
  • this straight-oil finishing composition is useful for treating fiber yarn.
  • Component (A) is a main component of the composition of the invention. Its function is to impart smoothness to the fiber yarn. It is recommended that the viscosity at 25° C. of the polydimethylsiloxane oil or liquid paraffin used in this component be within the range of 3 to 70 mm 2 /s, preferably 3 to 50 mm 2 /s, and even more preferably, 3 to 30 mm 2 /s. This is because, if the viscosity is below 3 mm 2 /s, the treated filament will have insufficient smoothness and if the viscosity exceeds 70 mm 2 /s, too much of the treatment agent will adhere to the fiber filament.
  • the molecular structure of the polydimethylsiloxane oil of component (A) may be linear, cyclic, or partially branched. In the case of a linear or partially branched molecular structure, it is recommended to cap the molecular terminals with groups such as trialkylsiloxy or hydroxyl groups.
  • the liquid paraffin useful in component (A) should have a high degree of purity, be colorless, and free of taste and odor.
  • Component (B) is a distinguishing component of the composition of the invention and comprises an organopolysiloxane resin which is compatible with component (A). It is required that 20 mole % or more of all siloxane units of this organopolysiloxane resin are represented by the formula C 3 H 7 SiO 3/2 and that each molecule of the aforementioned resin contain one or more silanol groups and one or more silicon-bonded alkoxy groups.
  • this component contains siloxane units of formula C 3 H 7 (HO) a (R′O) b SiO (3-a-b)/2 , where each R′ is an independently selected from alkyl group having 1 to 8 carbon atoms and alkyloxyalkylene group having 1 to 8 carbon atoms.
  • alkyl groups useful as R′ include methyl, ethyl, propyl, butyl, hexyl, and octyl.
  • alkyloxyalkylene groups useful as R′ include methoxyethylene, and ethoxyethylene.
  • the R′ groups are independently selected from all groups having 3 to 8 carbon atoms and alkyloxyalkylene groups having 3 to 8 carbon atoms, with alkyl groups having 3 to 8 carbon atoms being even more preferable.
  • alkyl groups having 3 to 8 carbon atoms being even more preferable.
  • Siloxane units of formula C 3 H 7 SiO 3/2 preferably comprise 20 to 95 mole % of all siloxane units, while siloxane units of formula C 3 H 7 (HO) a (R′O) b SiO (3-a-b)/2 preferably comprise 5 to 80 mole % of all siloxane units.
  • the sum of both siloxane units should be 40 mole % or more of all siloxane units and preferably should occupy 60 to 100 mole %.
  • the organopolysiloxane resin can be represented by the following average constitutional formula: (C 3 H 7 SiO 3/2 ) x [C 3 H 7 (HO) a (R′O) b SiO (3-a-b)/2 ] y ⁇ R c SiO (4-c/2) ⁇ z , where R′, a and b are as defined above; each R is an independently selected phenyl group, alkyl group having 1 to 10 carbon atoms, hydroxyl group, or alkoxy group. Examples of the alkyl group include methyl, ethyl, butyl, hexyl, octyl, and decyl.
  • the weight-average molecular weight of component (B) should be within the range of 800 to 20000, preferably 1000 to 8000.
  • component (B) examples include the following organopolysiloxane resins where a is 1 or 2 and b is 1 or 2: (C 3 H 7 SiO 3/2 ) 0.5 [C 3 H 7 (HO) a SiO (3-a)/2 ] 0.3 [C 3 H 7 (C 2 H 5 O) b SiO (3-b)/2 ] 0.2 , (C 3 H 7 SiO 3/2 ) 0.4 [C 3 H 7 (HO) a SiO (3-a)/2 ] 0.4 [C 3 H 7 (C 3 H 7 O) b SiO (3-b)/2 ] 0.2 , (C 3 H 7 SiO 3/2 ) 0.4 (CH 3 SiO 3/2 ) 0.2 [C 3 H 7 (HO) a SiO (3-a)/2 ] 0.32 [C 3H 7 O) b SiO (3-b)/2 ] 0.08 , (C 3 H 7 SiO 3/2 ) 0.4 ((CH 3 ) 2 SiO 2/2 ) 0.2 [C 3
  • Component (B) is obtained by hydrolyzing an organoalkoxysilane or organoalkoxysilanes.
  • an organoalkoxysilane or organoalkoxysilanes For example, it can be produced by hydrolyzing propyltrimethoxysilane, propyltriethoxysilane, propyltri(n-propoxy)silane, propyltri(i-propoxy)silane, or by co-hydrolyzing the aforementioned propylalkoxysilanes with various alkoxysilanes.
  • alkoxysilanes examples include methyltrimethoxysilane, methlyltriethoxysilane, methyltri(i-propoxy)silane, dimethyldimethoxysilane, and phenyltrimethoxysilane.
  • the propyltrichlorosilane can also be hydrolyzed in the presence of alcohol.
  • co-hydrolyzation can be carried out by adding methyltrichlorosilane, dimethyldichlorosilane, phenyltrichlorosilane, or similar chlorosilanes and methyltriethoxysilane, methyltriethoxysilane, methyltri(i-propoxy)silane, or similar methylalkoxysilane.
  • Alcohols suitable for these purposes include methanol, ethanol, n-propyl alcohol, i-propyl alcohol, butanol, methoxy ethanol, ethoxy ethanol, or similar alcohols.
  • hydrocarbon-type solvents which can also be concurrently used include toluene, xylene, or similar aromatic hydrocarbons; hexane, heptane, isooctane, or similar linear or partially branched saturated hydrocarbons; and cyclohexane, or similar aliphatic hydrocarbons.
  • Component (B) should be used in an amount of 0.5 to 100 parts by weight, preferably 10 to 70 parts by weight for each 100 parts by weight of component (A). If it is used in an amount smaller than the lower allowable limit, it will not be able to reveal its properties. If, however, it is used in an amount exceeding the upper recommended level, too much of component (B) will adhere to the treated product.
  • the composition of the invention is produced by merely mixing the aforementioned components (A) and (B). If necessary, in addition to the aforementioned components, the composition of the invention may be compounded with various additives. Such additives may include metal salts of higher fatty acids that antistick characteristics to the fiber yarn, for example magnesium stearate, zinc stearate, calcium stearate, and barium stearate. If necessary, the composition can be combined with anti-corrosive agents and charge-resistant agents. However, the composition should not contain ether-modified polyorganosiloxanes, such as polyorganosiloxane modified with ethylene oxide or polyorganosiloxane modified with propylene oxide.
  • Fiber yarn may be treated with the compositions, for example, by immersion in a treatment bath of the compositions of the invention followed by roll expression, or by bringing the running fiber yarn into contact with pick-up rolls.
  • the generally preferred add-on amount for the composition of this invention may be different depending on the type of the fiber yarn but it is preferably within the range of 0.05 to 9.0 wt. %.
  • Types of fiber yarn that can be treated with compositions of the invention include for example, natural fibers such as wool, silk, flax, cotton, angora, and mohair; regenerated fibers such as Rayon and Bemberg; semi-synthetic fibers such as acetate; and synthetic fibers such as polyester, polyamide, polyacrylonitrile, polyvinyl chloride, vinylon, polyethylene, polypropylene, and polyurethane (Spandex).
  • the word “yarn” refers to continuous filament thread, spun yarn, or tow.
  • the straight-oil treatment composition described above is characterized by improved antistatic properties, excellent compatibility with other components, and improved storage stability. This is achieved due to the use of the component (B) having a specific molecular structure. Furthermore, since component (B) can be synthesized at a relatively low cost, the composition of the invention can be advantageously used in commercial production.
  • Storage Stability The straight-oil fiber treatment composition was placed in a glass bottle and stored for 1 week at 25° C. and then was inspected visually. The storage stability was rated according to the following scale:
  • a four-neck flask equipped with a cooling pipe, thermometer, and a stirrer was loaded with 722 g of n-propyltrichlorosilane and 488 g of toluene. While the components were stirred, a mixture of 137 g of water and 317 g of isopropyl alcohol was added dropwise. Upon completion of the addition, the mixture was heated to 70° C. and stirred for 30 min. The mixture was then cooled, and the separated water layer was removed. The organic layer was then washed three times with water. The product was combined with 1000 g of water in which 10 g of sodium hydroxide was dissolved, and the components were mixed for 1 hour and washed three times with water.
  • a four-neck flask equipped with a cooling pipe, thermometer, and a stirrer was loaded with 722 g of n-propyltrichlorosilane and 488 g of toluene. While the components were stirred, a mixture of 137 g of water, 18 g of methyl-triisopropoxysilane, and 300 g of isopropyl alcohol was added dropwise. Upon completion of the addition, the mixture was heated to 70° C. and stirred for 30 min. The mixture was then cooled, and the separated water layer was removed. The organic layer was &en washed three times with water.
  • the product was combined with 1000 g of water in which 10 g of sodium hydroxide was dissolved, and the components were mixed for 1 hour and washed three times with water.
  • the cooling tube was replaced with a water separation tube, the product was heated, water was azeotropically removed, the solvent was removed by stripping, and, as result, a highly viscous organopolysiloxane was obtained.
  • a four-neck flask equipped with a cooling pipe, thermometer, and a stirrer was loaded with 722 g of n-propyltrichlorosilane and 488 g of toluene. While the components were stirred, 137 g of water was added dropwise. Upon completion of the addition, the mixture was heated to 70° C. and sired for 30 min. The mixture was then cooled, and the separated water layer was removed. The organic layer was then washed three times with water. The product was combined with 1000 g of water in which 10 g of sodium hydroxide was dissolved, and the components were mixed for 1 hour and washed three times with water.
  • the cooling tube was replaced with a water separation tube, the product was heated, water was azeotropically removed, the solvent was removed by stripping, and, as result, a highly viscous organopolysiloxane was obtained.
  • Analysis using 13 C-NMR, 29 Si-NMR and GPC showed that the obtained organopolysiloxane resin (TP-3) with a weight-average molecular weight of 5000 was represented by the following constitutional formula: ( n -C 3 H 7 SiO 3/2 ) 0.64 [n -C 3 H 7 (HO) a SiO (3-a)/2 ] 0.36 ,
  • a straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (TP-1) obtained in Synthesis Example 1 and 70 g of liquid paraffin having a viscosity of 12 mm 2 /s.
  • the obtained straight-oil fiber treatment composition comprised a transparent solution having a viscosity of 24 mm 2 /s, a specific gravity of 0.87, and a refractory index of 1.453. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured.
  • Volume resistivity was measured with the use of a volume-resistivity measurement instrument of Hewlett Packard Co. by a method for measuring volume resistivity (250V/1 min) specified by JIS C2101. All results of measurements and evaluation are shown in Table 1.
  • a straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (TP-1) obtained in Synthesis Example 1 and 70 g of liquid paraffin having a viscosity of 17 mm 2 /s.
  • the obtained straight-oil fiber treatment composition comprised a transparent solution having a viscosity of 30 mm 2 /s, a specific gravity of 0.91, and a refractory index of 1.456. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
  • a straight-oil fiber treatment composition was prepared by uniformly mixing 10 g of the organopolysiloxane resin (PIT-1) obtained in Synthesis Example 1 and 90 g of liquid paraffin having a viscosity of 12 mm 2 /s. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
  • a straight-oil fiber treatment composition was prepared by uniformly mixing 20 g of the organopolysiloxane resin (TP-1) obtained in Synthesis Example 1 and 80 g of liquid paraffin having a viscosity of 12 mm 2 /s. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
  • a straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (TP-2) obtained in Synthesis Example 2 and 70 g of liquid paraffin having a viscosity of 12 mm 2 /s.
  • the obtained straight-oil fiber treatment composition was transparent. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
  • a straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (TP-1) obtained in Synthesis Example 1 and 70 g of an oil of polydimethylsiloxane having both molecular terminals capped with trimethylsiloxy groups and having a viscosity of 10 mm 2 /s. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
  • a straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (IP-3) obtained in Synthesis Example 3 and 70 g of liquid paraffin having a viscosity of 12 mm 2 /s.
  • the obtained straight-oil fiber treatment composition comprises a semitransparent solution with a noticeable precipitation. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. All results of measurements and evaluation are shown in Table 1.
  • the straight-oil treatment composition of the invention which has aforementioned main components (A) and (B), is characterized by excellent component compatibility, storage stability, and anti-static properties.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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Abstract

The invention relates to a straight-oil finishing composition comprising (A) 100 parts by weight of a polydimethylsiloxane oil or liquid paraffin having a viscosity of 3 to 70 mm2/s at 25 centigrade temperature; and (B) 0.5 to 100 parts by weight of an organopolysiloxane resin, which contains silanol groups and silicon-bonded alkoxy groups and wherein 20 mole % or more of all siloxane units are siloxane units represented by formula C3H7SiO3/2. This composition is useful for treating fiber yarn.

Description

The invention relates to a straight-oil finishing composition useful for treating fiber yarn which has improved storage stability and antistatic properties, and a fiber yarn treated with the straight-oil finishing composition.
Various silicones find wide application in compositions of straight-oil type treatment agents which receive their name because they are free of any water or solvents. For example, it was proposed to use a mixture of polyamylsiloxane and polydimethylsiloxane as a lubricity-improving agent for Spandex or similar elastic filaments (see Japanese Patent Publication (hereinafter referred to as Kokoku) No. Sho 42-8438). However, this oil-type treatment agent utilizes expensive polyamylsiloxane. Furthermore, production of polyamylsiloxane may be accompanied by variations in the amount of silanol groups contained in this composition, as well as by variations in antistatic properties. A yarn-treating composition obtained by combining a dimethylsiloxane oil with the product of copolymerization of an MQ-type silicone resin and a DT-type silicone resin (see Kokoku No. Sho 63-12197) is also known. A drawback of the aforementioned product of copolymerization of the silicone resins is that copolymerization of the silicone resin is difficult to control and that viscosity and antistatic properties of the obtained oil-type treatment agent are subject to variations.
One object of the invention to provide a straight-oil finishing composition, which has excellent storage stability and antistatic properties.
The present invention relates to a straight-oil finishing composition comprising
  • (A) 100 parts by weight of a polydimethylsiloxane oil or liquid paraffin having a viscosity of 3 to 70 mm2/s at 25° C.; and
  • (B) 0.5 to 100 parts by weight of an organopolysiloxane resin which contains silanol groups and silicon-bonded alkoxy groups and 20 mole % or more of all siloxane units are represented by the formula C3H7SiO3/2.
Among other things, this straight-oil finishing composition is useful for treating fiber yarn.
Component (A) is a main component of the composition of the invention. Its function is to impart smoothness to the fiber yarn. It is recommended that the viscosity at 25° C. of the polydimethylsiloxane oil or liquid paraffin used in this component be within the range of 3 to 70 mm2/s, preferably 3 to 50 mm2/s, and even more preferably, 3 to 30 mm2/s. This is because, if the viscosity is below 3 mm2/s, the treated filament will have insufficient smoothness and if the viscosity exceeds 70 mm2/s, too much of the treatment agent will adhere to the fiber filament. The molecular structure of the polydimethylsiloxane oil of component (A) may be linear, cyclic, or partially branched. In the case of a linear or partially branched molecular structure, it is recommended to cap the molecular terminals with groups such as trialkylsiloxy or hydroxyl groups. The liquid paraffin useful in component (A) should have a high degree of purity, be colorless, and free of taste and odor.
Component (B) is a distinguishing component of the composition of the invention and comprises an organopolysiloxane resin which is compatible with component (A). It is required that 20 mole % or more of all siloxane units of this organopolysiloxane resin are represented by the formula C3H7SiO3/2 and that each molecule of the aforementioned resin contain one or more silanol groups and one or more silicon-bonded alkoxy groups. It is recommended that, in addition to the aforementioned siloxane units, this component contain siloxane units of formula C3H7 (HO)a(R′O)bSiO(3-a-b)/2, where each R′ is an independently selected from alkyl group having 1 to 8 carbon atoms and alkyloxyalkylene group having 1 to 8 carbon atoms. Examples of alkyl groups useful as R′ include methyl, ethyl, propyl, butyl, hexyl, and octyl. Examples of alkyloxyalkylene groups useful as R′ include methoxyethylene, and ethoxyethylene. Most preferably from the point of view of better compatibility with component (A), the R′ groups are independently selected from all groups having 3 to 8 carbon atoms and alkyloxyalkylene groups having 3 to 8 carbon atoms, with alkyl groups having 3 to 8 carbon atoms being even more preferable. In the above formula, 0<a≦2; 0<b≦2 and 0<(a+b)≦2. It is recommended that the amount of silanol groups contained in component (B) be greater than the amount of alkoxy groups so a>b. Siloxane units of formula C3H7SiO3/2 preferably comprise 20 to 95 mole % of all siloxane units, while siloxane units of formula C3H7(HO)a(R′O)bSiO(3-a-b)/2 preferably comprise 5 to 80 mole % of all siloxane units. The sum of both siloxane units should be 40 mole % or more of all siloxane units and preferably should occupy 60 to 100 mole %.
The organopolysiloxane resin can be represented by the following average constitutional formula:
(C3H7SiO3/2)x[C3H7(HO)a(R′O)bSiO(3-a-b)/2]y{RcSiO(4-c/2)}z,
where R′, a and b are as defined above; each R is an independently selected phenyl group, alkyl group having 1 to 10 carbon atoms, hydroxyl group, or alkoxy group. Examples of the alkyl group include methyl, ethyl, butyl, hexyl, octyl, and decyl. The most preferable from the point of view of compatibility with component (A) is methyl. Alkoxy groups may be the same as the aforementioned (R′O) groups; c is between 0 and 3; x>0, y>0, z≧0, (x+y+z)=1 and x/(x+y+z)≧0.2. In addition, it is recommended (x+y)/(x+y+z)≧0.4 and more preferably (x+y)/(x+y+z)≧0.6 The weight-average molecular weight of component (B) should be within the range of 800 to 20000, preferably 1000 to 8000. Examples of component (B) include the following organopolysiloxane resins where a is 1 or 2 and b is 1 or 2:
(C3H7SiO3/2)0.5[C3H7(HO)aSiO(3-a)/2]0.3[C3H7(C2H5O)bSiO(3-b)/2]0.2,
(C3H7SiO3/2)0.4[C3H7(HO)aSiO(3-a)/2]0.4[C3H7(C3H7O)bSiO(3-b)/2]0.2,
(C3H7SiO3/2)0.4(CH3SiO3/2)0.2[C3H7(HO)aSiO(3-a)/2]0.32[C3H 7O)bSiO(3-b)/2]0.08,
(C3H7SiO3/2)0.4((CH3)2SiO2/2)0.2[C3H7(HO)aSiO(3-a)/2]0.32[C3H7(C4H9O)bSiO(3-b)/2]0.08, and
(C3H7SiO3/2)0.4(C6H5SiO3/2)0.2[C3H7(HO)aSiO(3-a)/2]0.32[C3H7(C3H7O)bSiO(3-b)/2]0.08
Component (B) is obtained by hydrolyzing an organoalkoxysilane or organoalkoxysilanes. For example, it can be produced by hydrolyzing propyltrimethoxysilane, propyltriethoxysilane, propyltri(n-propoxy)silane, propyltri(i-propoxy)silane, or by co-hydrolyzing the aforementioned propylalkoxysilanes with various alkoxysilanes. Examples of these alkoxysilanes include methyltrimethoxysilane, methlyltriethoxysilane, methyltri(i-propoxy)silane, dimethyldimethoxysilane, and phenyltrimethoxysilane. The propyltrichlorosilane can also be hydrolyzed in the presence of alcohol. In this case, co-hydrolyzation can be carried out by adding methyltrichlorosilane, dimethyldichlorosilane, phenyltrichlorosilane, or similar chlorosilanes and methyltriethoxysilane, methyltriethoxysilane, methyltri(i-propoxy)silane, or similar methylalkoxysilane. Alcohols suitable for these purposes include methanol, ethanol, n-propyl alcohol, i-propyl alcohol, butanol, methoxy ethanol, ethoxy ethanol, or similar alcohols. Examples of hydrocarbon-type solvents which can also be concurrently used include toluene, xylene, or similar aromatic hydrocarbons; hexane, heptane, isooctane, or similar linear or partially branched saturated hydrocarbons; and cyclohexane, or similar aliphatic hydrocarbons.
Component (B) should be used in an amount of 0.5 to 100 parts by weight, preferably 10 to 70 parts by weight for each 100 parts by weight of component (A). If it is used in an amount smaller than the lower allowable limit, it will not be able to reveal its properties. If, however, it is used in an amount exceeding the upper recommended level, too much of component (B) will adhere to the treated product.
The composition of the invention is produced by merely mixing the aforementioned components (A) and (B). If necessary, in addition to the aforementioned components, the composition of the invention may be compounded with various additives. Such additives may include metal salts of higher fatty acids that antistick characteristics to the fiber yarn, for example magnesium stearate, zinc stearate, calcium stearate, and barium stearate. If necessary, the composition can be combined with anti-corrosive agents and charge-resistant agents. However, the composition should not contain ether-modified polyorganosiloxanes, such as polyorganosiloxane modified with ethylene oxide or polyorganosiloxane modified with propylene oxide.
Fiber yarn may be treated with the compositions, for example, by immersion in a treatment bath of the compositions of the invention followed by roll expression, or by bringing the running fiber yarn into contact with pick-up rolls. The generally preferred add-on amount for the composition of this invention may be different depending on the type of the fiber yarn but it is preferably within the range of 0.05 to 9.0 wt. %. Types of fiber yarn that can be treated with compositions of the invention include for example, natural fibers such as wool, silk, flax, cotton, angora, and mohair; regenerated fibers such as Rayon and Bemberg; semi-synthetic fibers such as acetate; and synthetic fibers such as polyester, polyamide, polyacrylonitrile, polyvinyl chloride, vinylon, polyethylene, polypropylene, and polyurethane (Spandex). As used herein, the word “yarn” refers to continuous filament thread, spun yarn, or tow.
The straight-oil treatment composition described above is characterized by improved antistatic properties, excellent compatibility with other components, and improved storage stability. This is achieved due to the use of the component (B) having a specific molecular structure. Furthermore, since component (B) can be synthesized at a relatively low cost, the composition of the invention can be advantageously used in commercial production.
The invention will now be described with reference to practical examples. In the examples hereinbelow, “parts” denotes “weight parts”, “%” denotes “weight %”, and the viscosity is the value at 25° C. The storage stability and compatibility were measured by the methods described below.
Compatibility—Immediately after preparation, 20 cc of the straight-oil fiber treatment composition was placed in a glass bottle, and its appearance was visually inspected. The compatibility was rated according to the following scale:
  • ∘: denotes homogeneous dissolution and transparency
  • Δ: denotes slight white turbidity
  • X: denotes significant white turbidity
Storage Stability—The straight-oil fiber treatment composition was placed in a glass bottle and stored for 1 week at 25° C. and then was inspected visually. The storage stability was rated according to the following scale:
  • ∘: denotes homogeneous dissolution and transparency
  • Δ: denotes slight separation and precipitation
  • X: denotes significant separation and precipitation
SYNTHESIS EXAMPLE 1
A four-neck flask equipped with a cooling pipe, thermometer, and a stirrer was loaded with 722 g of n-propyltrichlorosilane and 488 g of toluene. While the components were stirred, a mixture of 137 g of water and 317 g of isopropyl alcohol was added dropwise. Upon completion of the addition, the mixture was heated to 70° C. and stirred for 30 min. The mixture was then cooled, and the separated water layer was removed. The organic layer was then washed three times with water. The product was combined with 1000 g of water in which 10 g of sodium hydroxide was dissolved, and the components were mixed for 1 hour and washed three times with water. The cooling tube was replaced with a water separation tube, the product was heated, water was azeotropically removed, the solvent was removed by stripping, and, as result, a highly viscous organopolysiloxane was obtained. Analysis using 13C-NMR, 29Si-NMR, and GPC showed that the obtained organopolysiloxane resin (TP-1) with a weight-average molecular weight of 4800 was represented by the following constitutional formula:
(n-C3H7SiO3/2)0.58 [n-C3H7(HO)aSiO(3-a)/2]0.31 [n-C3H7O)bSiO(3-b)/2]0.11,
where a=1 or 2, and b=1 or 2.
SYNTHESIS EXAMPLE 2
A four-neck flask equipped with a cooling pipe, thermometer, and a stirrer was loaded with 722 g of n-propyltrichlorosilane and 488 g of toluene. While the components were stirred, a mixture of 137 g of water, 18 g of methyl-triisopropoxysilane, and 300 g of isopropyl alcohol was added dropwise. Upon completion of the addition, the mixture was heated to 70° C. and stirred for 30 min. The mixture was then cooled, and the separated water layer was removed. The organic layer was &en washed three times with water. The product was combined with 1000 g of water in which 10 g of sodium hydroxide was dissolved, and the components were mixed for 1 hour and washed three times with water. The cooling tube was replaced with a water separation tube, the product was heated, water was azeotropically removed, the solvent was removed by stripping, and, as result, a highly viscous organopolysiloxane was obtained. Analysis wing 13C-NMR, 29Si-NMR, and GPC showed that the obtained organopolysiloxane resin (TP-2) with a weight-average molecular weight of 4000 was represented by the following constitutional formula:
(n-C3H7SiO3/2)0.54(CH3SiO3/2)0.1 [n-C3H7(HO)aSiO(3-a)/2]0.27 [n-C3H7(i-C3H7O)bSiO(3-b)/2]0.09,
where a=1 or 2, and b=1 or 2.
SYNTHESIS EXAMPLE 3
A four-neck flask equipped with a cooling pipe, thermometer, and a stirrer was loaded with 722 g of n-propyltrichlorosilane and 488 g of toluene. While the components were stirred, 137 g of water was added dropwise. Upon completion of the addition, the mixture was heated to 70° C. and sired for 30 min. The mixture was then cooled, and the separated water layer was removed. The organic layer was then washed three times with water. The product was combined with 1000 g of water in which 10 g of sodium hydroxide was dissolved, and the components were mixed for 1 hour and washed three times with water. The cooling tube was replaced with a water separation tube, the product was heated, water was azeotropically removed, the solvent was removed by stripping, and, as result, a highly viscous organopolysiloxane was obtained. Analysis using 13C-NMR, 29Si-NMR and GPC showed that the obtained organopolysiloxane resin (TP-3) with a weight-average molecular weight of 5000 was represented by the following constitutional formula:
(n-C3H7SiO3/2)0.64 [n-C3H7(HO)aSiO(3-a)/2]0.36,
where a=1 or 2.
PRACTICAL EXAMPLE 1
A straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (TP-1) obtained in Synthesis Example 1 and 70 g of liquid paraffin having a viscosity of 12 mm2/s. The obtained straight-oil fiber treatment composition comprised a transparent solution having a viscosity of 24 mm2/s, a specific gravity of 0.87, and a refractory index of 1.453. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured with the use of a volume-resistivity measurement instrument of Hewlett Packard Co. by a method for measuring volume resistivity (250V/1 min) specified by JIS C2101. All results of measurements and evaluation are shown in Table 1.
PRACTICAL EXAMPLE 2
A straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (TP-1) obtained in Synthesis Example 1 and 70 g of liquid paraffin having a viscosity of 17 mm2/s. The obtained straight-oil fiber treatment composition comprised a transparent solution having a viscosity of 30 mm2/s, a specific gravity of 0.91, and a refractory index of 1.456. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
PRACTICAL EXAMPLE 3
A straight-oil fiber treatment composition was prepared by uniformly mixing 10 g of the organopolysiloxane resin (PIT-1) obtained in Synthesis Example 1 and 90 g of liquid paraffin having a viscosity of 12 mm2/s. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
PRACTICAL EXAMPLE 4
A straight-oil fiber treatment composition was prepared by uniformly mixing 20 g of the organopolysiloxane resin (TP-1) obtained in Synthesis Example 1 and 80 g of liquid paraffin having a viscosity of 12 mm2/s. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
PRACTICAL EXAMPLE 5
A straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (TP-2) obtained in Synthesis Example 2 and 70 g of liquid paraffin having a viscosity of 12 mm2/s. The obtained straight-oil fiber treatment composition was transparent. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
PRACTICAL EXAMPLE 6
A straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (TP-1) obtained in Synthesis Example 1 and 70 g of an oil of polydimethylsiloxane having both molecular terminals capped with trimethylsiloxy groups and having a viscosity of 10 mm2/s. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
COMPARATIVE EXAMPLE 1
A straight-oil fiber treatment composition was prepared by uniformly mixing 30 g of the organopolysiloxane resin (IP-3) obtained in Synthesis Example 3 and 70 g of liquid paraffin having a viscosity of 12 mm2/s. The obtained straight-oil fiber treatment composition comprises a semitransparent solution with a noticeable precipitation. Compatibility and storage stability of the obtained straight-oil fiber treatment composition were measured. All results of measurements and evaluation are shown in Table 1.
COMPARATIVE EXAMPLE 2
Storage stability was measured for a strait-oil fiber treatment composition that comprised 100 g only of liquid paraffin of a viscosity of 12 mm2/s. Volume resistivity was measured by the same method as in Practical Example 1. All results of measurements and evaluation are shown in Table 1.
TABLE 1
(A) (B) Storage Volume
Type Content % Type Content % Compatibility Stability Resistivity Evaluation
Pr. Ex. 1 A-1 70 TP-1 30 ◯ ◯ 2 × 1013 Good
Pr. Ex. 2 A-2 70 TP-1 30 ◯ ◯ 2 × 1013 Good
Pr. Ex. 3 A-1 90 TP-1 10 ◯ ◯ 4 × 1013 Good
Pr. Ex. 4 A-1 80 TP-1 20 ◯ ◯ 3 × 1013 Good
Pr. Ex. 5 A-1 70 TP-2 30 ◯ ◯ 3 × 1013 Good
Pr. Ex. 6 A-3 70 TP-1 30 ◯ ◯ 3 × 1013 Good
Comp. Ex. 1 A-1 70 TP-3 30 Δ Δ — Unsatisfactory (insufficient
compatibility and storage stability)
Comp. Ex. 2 A-1 100 — 0 — ◯ 4 × 1014 Unsatisfactory (insufficient
antistatic properties)
* Types of component (A):
A-1: liquid paraffin of 12 mm2/s viscosity
A-2: liquid paraffin of 17 mm2/s viscosity
A-3: polydimethylsiloxane oil of 10 mm2/s viscosity
The straight-oil treatment composition of the invention, which has aforementioned main components (A) and (B), is characterized by excellent component compatibility, storage stability, and anti-static properties.

Claims (13)

1. A straight-oil finishing composition comprising
(A) 100 parts by weight of a polydimethylsiioxane oil or liquid paraffin having a viscosity of 3 to 70 mm2/s at 25° C.; and
(B) 0.5 to 100 parts by weight of an organopolysiloxane resin, which contains silanol groups and silicon-bonded alkoxy groups, wherein 20 mole % or more of all siloxane units are siloxane units represented by formula C3H7SiO3/2, and wherein the amount of silanol groups is greater than the amount of the silicon-bonded alkoxy groups.
2. The straight-oil finishing composition according to claim 1, where said component (A) is liquid paraffin.
3. A straight-oil finishing composition comprising
(A) 100 parts by weight of a polydimethylsiioxane oil or liquid paraffin having a viscosity of 3 to 70 mm2/s at 25° C.: and
(B) 0.5 to 100 parts by weight of an organopolysiloxane resin, which contains silanol groups and silicon-bonded alkoxy groups, wherein 20 mole % or more of all siloxane units are siloxane units represented by formula C3H7SiO3/2, and wherein said silicon-bonded alkoxy groups are alkoxy groups having 3 to 8 carbon atoms.
4. The straight-oil finishing composition according to claim 3, where said component (A) is liquid paraffin.
5. A fiber yarn treated with the straight-oil finishing composition of claim 3.
6. A straight-oil finishing composition comprising
(A) 100 parts by weight of a polydimethylsiioxane oil or liquid paraffin having a viscosity of 3 to 70 mm2/s at 25° C.; and
(B) 0.5 to 100 parts by weight of an organopolysiloxane resin, which contains silanol groups and silicon-bonded alkoxy groups and wherein 20 mole % or more of all siloxane units are siloxane units represented by formula C3H7SiO3/2; and
where said component (B) contains both siloxane units represented by formula C3H7SiO3/2 and C3H7(HO)a(R′O)bSiO(3-a-b)/2, wherein 20-95 mole % of all siloxane units are siloxane units represented by formula C3H7SiO3/2 and 5-80 mole % of all siloxane units are siloxane units represented by formula

C3H7(HO)a(R′O)bSiO(3-a-b)/2,
where each R′ is independently selected from alkyl groups having 1 to 8 carbon atoms and alkyloxyalkylene groups having 1 to 8 carbon atoms, 0<a≦2, 0<b≦2, 0<(a+b)≦2.
7. The straight-oil finishing composition according to claim 6, where said component (A) is liquid paraffin.
8. A fiber yarn treated with the straight-oil finishing composition of claim 6.
9. A straight-oil finishing composition comprising
(A) 100 parts by weight of a polydimethylsiioxane oil or liquid paraffin having a viscosity of 3 to 70 mm2/s at 25° C.; and
(B) 0.5 to 100 parts by weight of an organopolysiloxane resin, which contains silanol groups and silicon-bonded alkoxy groups, wherein 20 mole % or more of all siloxane units are siloxane units represented by formula C3H7SiO3/2, and where said component (B) is represented by the following average constitutional formula:

(C3H7SiO3/2)x[C3H7(HO)a(R′O)b SiO(3-a-b)/2]y{RcSiO(4-c/2)}z,
where each R′ is independently selected from alkyl groups having 1 to 8 carbon atoms and alkyloxyalkylene groups having 1 to 8 carbon atoms, and each R is independently selected from phenyl groups, alkyl groups having 1 to 10 carbon atoms, hydroxyl groups, and alkoxy groups, 0<a≦2, 0<b≦2, 0<(a+b)≦2, c is between 0 and 3, x>0, y>0, z≧0, (x+y+z)=1, and x/(x+y+z)≧0.2.
10. The straight-oil finishing composition according to claim 9, where said component (A) is liquid paraffin.
11. A fiber yarn treated with the straight-oil finishing composition of claim 9.
12. A fiber yarn treated with the straight-oil finishing composition comprising
(A) 100 parts by weight of a polydimethylsiioxane oil or liquid paraffin having a viscosity of 3 to 70 mm2/s at 25° C.; and
(B) 0.5 to 100 parts by weight of an organopolysiloxane resin, which contains silanol groups and silicon-bonded alkoxy groups and wherein 20 mole % or more of all siloxane units are siloxane units represented by formula C3H7SiO3/2.
13. A fiber yarn according to claim 12, where said component (A) is liquid paraffin.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080277432A1 (en) * 2007-05-08 2008-11-13 Willi Horcher Assist device for doffing stockings
US11541090B2 (en) 2021-05-26 2023-01-03 Ningbo Rhysuair Biotechnology Co., Ltd. Composition for eliminating household pet allergens

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018522145A (en) * 2015-05-22 2018-08-09 プリマロフト，インコーポレイテッド Silicone-treated synthetic filament yarn
WO2024122372A1 (en) * 2022-12-08 2024-06-13 松本油脂製薬株式会社 Elastic fiber treatment agent and use thereof
JP7259127B1 (en) 2022-12-08 2023-04-17 松本油脂製薬株式会社 Elastic fiber treatment agent and its use

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3294737A (en) 1963-12-23 1966-12-27 Gen Electric Organopolysiloxanes
US3296063A (en) 1963-11-12 1967-01-03 Du Pont Synthetic elastomeric lubricated filament
JPS428438Y1 (en) 1964-03-10 1967-05-02
US3684756A (en) * 1970-07-07 1972-08-15 Stauffer Wacker Silicone Corp Mold release compositions from mixtures of silicone resins and siloxane fluids
US3819745A (en) 1972-03-27 1974-06-25 Dow Corning Coatings giving controlled release
US3836647A (en) * 1970-10-22 1974-09-17 Dow Corning Wash-resistant skin preparation
US3872038A (en) * 1973-12-03 1975-03-18 Stauffer Chemical Co Aqueous based release composition
US4087478A (en) 1976-04-14 1978-05-02 Dow Corning Corporation Siloxane copolymers and thread finisher prepared therewith
JPS6312197A (en) 1986-07-03 1988-01-19 富士通株式会社 Cooler
US6245431B1 (en) * 1999-09-20 2001-06-12 General Electric Company Bakeware release coating
US6767982B2 (en) * 2000-11-14 2004-07-27 Degussa Ag Continuous manufacturing process for organoalkoxysiloxanes
US6841197B2 (en) * 2000-11-14 2005-01-11 Degussa Ag n-Propylethoxysiloxanes, their preparation and use
US7019069B2 (en) * 2001-02-09 2006-03-28 Dow Corning Toray Silicone Co., Ltd. Silicone resin composition for water repellent coating

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296063A (en) 1963-11-12 1967-01-03 Du Pont Synthetic elastomeric lubricated filament
US3294737A (en) 1963-12-23 1966-12-27 Gen Electric Organopolysiloxanes
JPS428438Y1 (en) 1964-03-10 1967-05-02
US3684756A (en) * 1970-07-07 1972-08-15 Stauffer Wacker Silicone Corp Mold release compositions from mixtures of silicone resins and siloxane fluids
US3836647A (en) * 1970-10-22 1974-09-17 Dow Corning Wash-resistant skin preparation
US3819745A (en) 1972-03-27 1974-06-25 Dow Corning Coatings giving controlled release
US3872038A (en) * 1973-12-03 1975-03-18 Stauffer Chemical Co Aqueous based release composition
US4087478A (en) 1976-04-14 1978-05-02 Dow Corning Corporation Siloxane copolymers and thread finisher prepared therewith
JPS6312197A (en) 1986-07-03 1988-01-19 富士通株式会社 Cooler
US6245431B1 (en) * 1999-09-20 2001-06-12 General Electric Company Bakeware release coating
US6767982B2 (en) * 2000-11-14 2004-07-27 Degussa Ag Continuous manufacturing process for organoalkoxysiloxanes
US6841197B2 (en) * 2000-11-14 2005-01-11 Degussa Ag n-Propylethoxysiloxanes, their preparation and use
US7019069B2 (en) * 2001-02-09 2006-03-28 Dow Corning Toray Silicone Co., Ltd. Silicone resin composition for water repellent coating

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080277432A1 (en) * 2007-05-08 2008-11-13 Willi Horcher Assist device for doffing stockings
US11541090B2 (en) 2021-05-26 2023-01-03 Ningbo Rhysuair Biotechnology Co., Ltd. Composition for eliminating household pet allergens

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